Answered: Use strain energy increments in the OWL…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Use strain energy increments in the OWL Table Reference (see References button, Strain Energy Increments) to calculate the energy difference between the two chair conformations of the compound below.

Specify substituent positions (axial or equatorial) in the more stable chair.

Estimate the percent of the more stable chair at equilibrium at 25°C.

(To determine the percent of the more stable chair at equilibrium, first calculate Keq, and then use this value to find the percentage.)

Use the References to access important values if needed for this question.
a. Use strain energy increments in the OWL Table Reference (see References button, Strain Energy Increments) to calculate the energy difference
between the two chair conformations of the compound below.
b. Specify substituent positions (axial or equatorial) in the more stable chair.
c. Estimate the percent of the more stable chair at equilibrium at 25°C.
(To determine the percent of the more stable chair at equilibrium, first calculate Keq, and then use this value to find the percentage.)
CH3
Answers:
a. The energy difference is
b. In the more stable chair:
The vinyl(ethenyl) group is in the
position.
position.
o The methyl group is in the (
c. At 25°C the equilibrium percent of the more stable chair conformation is approximately
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Retry Entire Group 8 more group attempts remaining
kJ/mol.

Axial Strain Energies for Monosubstituted Cyclohexanesa, D
This table gives the sum of the values for the 1,3 diaxial interactions of the substituent with two hydrogen atoms.
Substituent(solvent)
kJ/mol
kcal/mol
-CH3
7.3
1.7
-CH₂CH3
7.5
1.8
-CH(CH3)2
9.2
2.2
-C(CH3)3
20
4.8
phenyl
11.7
2.8
cyclohexyl
9.2
2.2
-CH=CH₂
6.2
1.5
-CCH, ethynyl
2.1
0.5
-CHO
3.0
0.7
-COCH 3
5.1
1.2
-CO₂H
5.9
1.4
-CO,CH,CH3
5.0
1.2
-Cl
2.5
0.6
-Br
2.5
0.6
-CN, cyano
0.8
0.2
-OH (cyclohexane)
2.5
0.6
-OH (isopropanol)
4.0
1.0
-OCH3
2.5
0.6
-NH₂ (toluene)
5.2
1.2
-NH2 (CH3OCH₂CH₂OH/H₂O)
7.1
1.7

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